Hotels Near
Old Town Winchester

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Featured Old Town Winchester Hotels

The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,006 reviews)
"Beautiful hotel, super easy check in, restaurant on the property is Unos Pizzeria, just one block away is Old Town and we had an enjoyable evening strolling that area after dinner. We’ve already booked another stay for ‘our stop on the way home.’"

Reviewed on Mar 31, 2025

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,891 reviews)
"The room layout is unique and we love it."

Reviewed on Mar 29, 2025

La Quinta Inn & Suites by Wyndham Winchester
Spark by Hilton Winchester
Spark by Hilton Winchester
3 out of 5
150 Wingate Dr, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,002 reviews)
"Good comfortable stay, woukd use again"

Reviewed on Mar 28, 2025

Spark by Hilton Winchester
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,002 reviews)
"All good!"

Reviewed on Mar 29, 2025

Comfort Inn & Suites
Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,167 reviews)
"Very clean."

Reviewed on Mar 31, 2025

Microtel Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,001 reviews)
"Very nice staff. Quiet and very clean place."

Reviewed on Mar 24, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
DoubleTree by Hilton Front Royal Blue Ridge Shadows
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4 out of 5
111 Hospitality Drive, Front Royal, VA
Fully refundableReserve now, pay when you stay
Stay at this 4-star golf hotel in Front Royal. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms in our ...
8.8/10 Excellent! (999 reviews)
Comfy but don’t eat at houlihans
"Very comfy and quiet…restaurant that’s attached was gross but hotel was amazing"

Reviewed on Mar 23, 2025

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.2/10 Very Good! (1,105 reviews)
"Service was friendly & quick Room was super clean & smelled clean I felt safe because I observed desk clerk watching activity on cameras"

Reviewed on Mar 30, 2025

Travelodge by Wyndham Winchester
Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
140 Costello Dr, Winchester, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
"These exterior of the hotel was very clean the lobby way and entranceway were very clean. Check in staff was very courteous. When we opened our room, the bathroom door and frame of the bathroom door was in very poor condition. It worked, but it had scraped up flaking paint it was not Presentable. ..."

Reviewed on Mar 23, 2025

Sleep Inn & Suites
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,003 reviews)
"Fromt desk personnel were excellent."

Reviewed on Mar 29, 2025

Country Inn & Suites by Radisson, Winchester, VA
SpringHill Suites by Marriott Winchester
SpringHill Suites by Marriott Winchester
2.5 out of 5
280 MARKET STREET, Winchester, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (572 reviews)
"Location"

Reviewed on Mar 20, 2025

SpringHill Suites by Marriott Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley
Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,004 reviews)
"We liked everything!"

Reviewed on Mar 27, 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels in Old Town Winchester

Winchester is a city that has a lot going on, but you have your sights set on Old Town Winchester. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Old Town Winchester has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Old Town Winchester hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Winchester so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Old Town Winchester underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Old Town Winchester city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Old Town Winchester cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Old Town Winchester at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $69
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Old Town Winchester hotel you want, book it, and never look back. Because your great escape is ahead of you.